CA1038882A - Acide m-benzoyl hydratropique - Google Patents
Acide m-benzoyl hydratropiqueInfo
- Publication number
- CA1038882A CA1038882A CA254,098A CA254098A CA1038882A CA 1038882 A CA1038882 A CA 1038882A CA 254098 A CA254098 A CA 254098A CA 1038882 A CA1038882 A CA 1038882A
- Authority
- CA
- Canada
- Prior art keywords
- benzoyl
- acid
- hydratropic
- product
- condensation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- DKYWVDODHFEZIM-UHFFFAOYSA-N ketoprofen Chemical compound OC(=O)C(C)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1 DKYWVDODHFEZIM-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000009833 condensation Methods 0.000 claims abstract description 5
- 230000005494 condensation Effects 0.000 claims abstract description 5
- YTVQIZRDLKWECQ-UHFFFAOYSA-N 2-benzoylcyclohexan-1-one Chemical compound C=1C=CC=CC=1C(=O)C1CCCCC1=O YTVQIZRDLKWECQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003377 acid catalyst Substances 0.000 claims abstract description 4
- 238000010438 heat treatment Methods 0.000 claims abstract description 4
- 229940107700 pyruvic acid Drugs 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- 150000002148 esters Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims abstract 4
- 239000011541 reaction mixture Substances 0.000 claims abstract 3
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 239000000047 product Substances 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 14
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- -1 secondary amine salt Chemical class 0.000 claims description 3
- RFSHNKCWSIXKFY-UHFFFAOYSA-N 7-benzoyl-3-methyl-5,6-dihydro-4h-1-benzofuran-2-one Chemical compound C=12OC(=O)C(C)=C2CCCC=1C(=O)C1=CC=CC=C1 RFSHNKCWSIXKFY-UHFFFAOYSA-N 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000005899 aromatization reaction Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 150000002596 lactones Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229910052681 coesite Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229910052906 cristobalite Inorganic materials 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 2
- 229940117360 ethyl pyruvate Drugs 0.000 description 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 229910052682 stishovite Inorganic materials 0.000 description 2
- 229910052905 tridymite Inorganic materials 0.000 description 2
- DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical class CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 206010012335 Dependence Diseases 0.000 description 1
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000008365 aromatic ketones Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 description 1
- 150000005332 diethylamines Chemical class 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000004728 pyruvic acid derivatives Chemical class 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT49925/75A IT1035947B (it) | 1975-06-05 | 1975-06-05 | Sintesi dell acido m. benzoil idratropico |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1038882A true CA1038882A (fr) | 1978-09-19 |
Family
ID=11271866
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,098A Expired CA1038882A (fr) | 1975-06-05 | 1976-06-04 | Acide m-benzoyl hydratropique |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4097522A (fr) |
| JP (1) | JPS51149251A (fr) |
| AR (1) | AR208604A1 (fr) |
| BE (1) | BE842471A (fr) |
| CA (1) | CA1038882A (fr) |
| CH (1) | CH630054A5 (fr) |
| DE (1) | DE2624177A1 (fr) |
| ES (1) | ES448524A1 (fr) |
| FI (1) | FI761484A (fr) |
| FR (2) | FR2319620A1 (fr) |
| GB (1) | GB1515614A (fr) |
| HU (1) | HU172925B (fr) |
| IT (1) | IT1035947B (fr) |
| NL (1) | NL7605889A (fr) |
| SU (1) | SU639441A3 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4154962A (en) * | 1975-01-21 | 1979-05-15 | Aziende Chimiche Riunite Angelini Francesco A.C.R.A.F. S.P.A. | Synthesis of hydratropic acid and some of its alkyl derivatives |
| GB2000502B (en) * | 1977-06-22 | 1982-01-06 | Acraf | Process for the production of m-benzoyl hydratropic acid |
| DD141422A5 (de) * | 1978-01-27 | 1980-04-30 | Schering Ag | Verfahren zur herstellung von phenylessigsaeure-derivaten |
| JPH07100678B2 (ja) * | 1987-03-12 | 1995-11-01 | 日本石油化学株式会社 | α−（３−ベンゾイルフエニル）プロピオン酸の製造方法 |
| JP2782080B2 (ja) * | 1989-03-06 | 1998-07-30 | 日本石油化学株式会社 | α―（３―ベンゾイルフェニル）プロピオン酸誘導体の製造方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE622405C (de) * | 1933-02-09 | 1935-12-12 | Byk Guldenwerke Chem Fab Akt G | Verfahren zur Darstellung ungesaettigter Laktone der alicyclischen Reihe |
| FR2043472A1 (fr) * | 1969-05-19 | 1971-02-19 | Rhone Poulenc Sa |
-
1975
- 1975-06-05 IT IT49925/75A patent/IT1035947B/it active
-
1976
- 1976-05-26 FI FI761484A patent/FI761484A/fi not_active Application Discontinuation
- 1976-05-27 GB GB22103/76A patent/GB1515614A/en not_active Expired
- 1976-05-28 US US05/690,832 patent/US4097522A/en not_active Expired - Lifetime
- 1976-05-29 DE DE19762624177 patent/DE2624177A1/de not_active Withdrawn
- 1976-06-01 NL NL7605889A patent/NL7605889A/xx not_active Application Discontinuation
- 1976-06-01 BE BE167547A patent/BE842471A/fr unknown
- 1976-06-02 AR AR263486A patent/AR208604A1/es active
- 1976-06-03 ES ES448524A patent/ES448524A1/es not_active Expired
- 1976-06-04 HU HU76AI00000258A patent/HU172925B/hu unknown
- 1976-06-04 SU SU762365909A patent/SU639441A3/ru active
- 1976-06-04 CA CA254,098A patent/CA1038882A/fr not_active Expired
- 1976-06-04 CH CH709776A patent/CH630054A5/it not_active IP Right Cessation
- 1976-06-04 JP JP51066379A patent/JPS51149251A/ja active Granted
- 1976-06-08 FR FR7617286A patent/FR2319620A1/fr active Granted
- 1976-11-09 FR FR7633716A patent/FR2319636A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| US4097522A (en) | 1978-06-27 |
| FR2319636B1 (fr) | 1981-06-26 |
| JPS51149251A (en) | 1976-12-22 |
| NL7605889A (nl) | 1976-12-07 |
| AR208604A1 (es) | 1977-02-15 |
| IT1035947B (it) | 1979-10-20 |
| FR2319620A1 (fr) | 1977-02-25 |
| DE2624177A1 (de) | 1976-12-23 |
| JPS5761258B2 (fr) | 1982-12-23 |
| BE842471A (fr) | 1976-12-01 |
| SU639441A3 (ru) | 1978-12-25 |
| ES448524A1 (es) | 1977-07-01 |
| GB1515614A (en) | 1978-06-28 |
| FI761484A (fr) | 1976-12-06 |
| CH630054A5 (it) | 1982-05-28 |
| HU172925B (hu) | 1979-01-28 |
| FR2319620B1 (fr) | 1983-01-28 |
| FR2319636A1 (fr) | 1977-02-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2020037596A (ja) | カンナビジオール及びδ−９−テトラヒドロカンナビノールの生成のためのプロセス | |
| CN114981235A (zh) | 大麻素衍生物、前体和用途 | |
| Borovika et al. | Chiral brønsted acid-catalyzed enantioselective ionic [2+ 4] cycloadditions | |
| CA1038882A (fr) | Acide m-benzoyl hydratropique | |
| Ingold et al. | CXCV.—Experiments on the synthesis of the polyacetic acids of methane. Part VII. iso-Butylene-α γγ-′ tricarboxylic acid and methanetetra-acetic acid | |
| JPH0250909B2 (fr) | ||
| CN112479967A (zh) | 胆绿素类化合物及其制备方法和用途 | |
| JPS5814434B2 (ja) | τ−ピロン製造のための中間体 | |
| CA2684476A1 (fr) | Procede de production du trans-2-aminocyclohexanol optiquement actif et d'un intermediaire du trans-2-aminocyclohexanol optiquement actif | |
| KR910009415B1 (ko) | 비스(펜옥시)아세틸 nn-디메틸 아미드의 제조방법 | |
| Simonsen | CLXXV.—Syntheses with the aid of monochloromethyl ether. Part I. The action of monochloromethyl ether on the sodium derivatives of ethyl malonate and ethyl iso propylmalonate | |
| SU615073A1 (ru) | Способ получени 1,3-ди(фурил-2 -) пропенона | |
| Cromartie et al. | 186. Melanin and its precursors. Part IV. Synthesis of β-3: 4-dihydroxy-2-and-5-methylphenylalanine | |
| SU277770A1 (ru) | Способ получения замещенных а^'р-бутенолидов | |
| JPH0848677A (ja) | ベンゾ複素環系の化合物、その製造方法及びそれを含有する組成物 | |
| SU281465A1 (ru) | Способ получения эфиров м-ацил-з- (о-алкилметилфосфонил)-цистеина | |
| GB2181432A (en) | Chemical process | |
| SU899565A1 (ru) | Способ получени @ -оксифосфиновых кислот | |
| KR100195888B1 (ko) | 디엘-3-메칠-시크로펜타데칸-1-온의 제조방법 | |
| SU379557A1 (ru) | Способ получения 2,4-диалкил-2,4- -динитропентандиолов-1,5 | |
| SU697506A1 (ru) | Способ получени 1-метил-7-формилиндола | |
| SU612924A1 (ru) | Способ получени 5,5-диметил-3фенилциклогексен-2-она | |
| SU554674A1 (ru) | Способ получени (-) - о метил-дАуРициНА | |
| EP0101003B1 (fr) | Procédé pour la préparation d'un dérivé de l'oxo-4-tétrahydro-4,5,6,7-benzofuranne | |
| SU1648947A1 (ru) | Способ получени метилзамещенных оксазолов |